Dropbox’s Akhil Gupta on ‘Brutal Prioritization’

This week’s episode is all about magic pockets, nickels, cupcakes, and brutal prioritization. It’s a conversation with Akhil Gupta, the general manager and VP of enterprise at Dropbox.

Before that, he was the VP of engineering and the head of infrastructure -- running a 500-person engineering team that helped create the technical foundation for the Dropbox we know today.

Steve and Quentin will talk with Akhil about how Dropbox scaled reliably from 2,000 users in 2008 to hundreds of millions of registered users today.

Back in 2012, when Akhil first joined the company from Google, there were 30 engineers. Dropbox had emerged as a leading cloud storage provider, but it faced a clear choice: should it build its own storage or rely on the public cloud? Enter "Magic Pocket."

And that technical challenge forced him to adopt a simple philosophy: brutal prioritization.

“My anxiety always is when you get too many people in a company, you start creating problems and you start losing focus because you have so much new energy, you are growing fast and you can say, let me solve every single problem. So I wanted to give a signal to the team saying, we need to always prioritize. And prioritization is hard, prioritization is painful. And hence the word brutal,” says Akhil.

This podcast is produced by Post Script Audio in collaboration with General Catalyst.